Wake Up
by SirGawain99
Summary: Dean wants Oliver to wake up, but it seems like he'll never leave his coma, and when he does, is he even the same person? Sequel to Ink.
1. Chapter 1

[text: Jade] Any news on Oliver?

[text: Sam] Still comatose. I said I would tell you if there was a change.

[text: Jade] Dean's been asking, I have to tell him something.

[text: Sam] I don't know Sam, I'm sorry.

Jade let out a long sigh, staring at her phone. It had been nearly four months since Oliver had entered his coma. Since then Jade had been in contact with Sam. He had been a rock for her, someone who understood the pain she was going through.

[text: Sam] I have to go open up the shop, talk to ya later.

Her days were a collection of the same few activities, open the shop, run the shop, go to sleep. Occasionally she went out to dinner with Marlow, who tried to get Jade out more. It didn't work.

One day while running the shop Jade froze when she saw who walked in the door. "Dean! I wasn't expecting you to visit," she said, trying to hide the shaking in her voice and failing miserably. "What are you doing here?" She glanced between Dean and Sam, desperately looking for an explanation from the latter.

"Cut the bullshit Jade, where's Oliver?" Dean demanded, his voice gruff.

She looked over at Sam, desperate for some form of help.

Sam looked away, letting out a little sigh. "I told him Jade. I can't just keep lying forever," he said.

"Dean I'm sorry, but he wouldn't have wanted you to know," she said, her voice breaking slightly.

"Oh so you thought that you could just keep lying forever right? That this would just all disappear? Jesus you are stupid," Dean spat out, stepping forward until Jade backed into the counter. "You had no right not to tell me! No right!"

Jade stayed there, squeezing her eyes shut and just breathing deeply.

"Dean, calm down," Sam said, taking a step towards his brother.

"No Sam! She knew how I felt about him," he said, rage barely contained.

"Dean what are you talking about?" Sam asked, stepping closer to his brother. He looked over at Jade, who seemed to have calmed herself down enough to open her eyes again. If he had learned anything about Jade in the past few months of texting her, it was that she was anything but a stable person. He doubted that the shouting was helping that.

"I... Oliver and I had a thing. He was more than just some guy Sam," Dean explained. He hadn't planned on coming out today, and he sure as hell didn't think that it would happen because his almost boyfriend was in a coma. "Sam I really liked him. I wanted to come back here just to see him, but you always came up with a case, always had a reason why we couldn't. Guess she had something to do with that, huh?" He jabbed his thumb at Jade.

Sam stared at his brother for a moment. He wasn't surprised by the fact that Dean was bisexual, he'll be had suspected it for ages himself, but it was different to actually hear it coming out of his brother's mouth. "No, don't-"

"I asked him to Dean, please don't be mad at Sam for this," she said quietly. "But the full truth is they really don't think that Oliver is ever going to wake up. He wouldn't want to bring you down like that. I just wanted to make sure that you were happy, that you could move on easy, like he would have wanted you to."

Dean nodded a little and rubbed his face. He was getting too old for this. What he was getting too old for he wasn't sure, but there was certainly some part of him that desperately needed a break from everything he went through on a weekly basis. "Yeah uh... could we visit him? I just really want to see him for myself now that I know."

Jade nodded and offered him a thin smile. "Promise me you won't try anything stupid to wake him up? Like for sure no selling your soul," she joked, smirking a little at the surprised look on Dean's face. "Sam told me, I mean we did talk about stuff besides lying to you."

He let out a small laugh. There wasn't any joy in it, but it was something. "Nice, real nice... let's get going, I can drive us there."

As they walked out Sam looked at his brother. "Do you want to talk about well..."

"I like guys and I like girls, there isn't much to it Sammy," Dean said and shrugged. "Just how I am."

Sam nodded as the three of them got in the car, feeling like he was just a bit closer to his brother now.

The room was almost exactly the same as it had been before. The only difference was a few books on a desk near the bed. When Dean flipped through them, just doing something for the sake of doing it, he saw Jade had written her name on the inside cover of each one. "So is there any news at all about him?" Dean asked, looking at her and raising an eyebrow.

"The doctors are pretty confident that he won't die now," she said softly, sitting in her usual seat by her brother. "They're also pretty confident that he won't be waking up anytime soon."

Dean sat down beside her and patted her arm. She shrunk away from his touch for a moment, but relaxed just a moment later. "But what do you think? Do you think he's gonna get up?"

"My brother is a witch, an asshole, and a tough son of a bitch, but honestly? I have no clue," she said and sighed, hanging her head. "And before you ask about spells, Marlow and I have tried just about everything."

"Well, maybe he just needs some more time," Dean said, gears already turning in his mind to figure out some way to wake Oliver back up. He wanted to be there when it happened. When it happened, not if it happened. He was hopelessly optimistic when it came to Oliver.

"I hope you're right Dean," she said softly. "I've been praying every day, but I feel like I'm not getting anywhere with it. You'd think that after meeting an angel that I might have a bit more faith, but hey, why would anything I do make sense?"

"Maybe I could ask Cas for help. I mean he can heal people just like that," he said, snapping his fingers. It would be worth a shot. "It isn't like Oliver has done anything wrong."

"Besides be a witch," Sam pointed out. "I'm pretty sure that they used to set them on fire back in the day."

"Yeah but this is Cas, he'd do this for us," Dean said stubbornly. "And just give him those puppy dog eyes of yours, how can he say no?"

Jade laughed a little under her breath, trying to hide just how much better she felt being around other people. Maybe the constant isolation of the shop wasn't as healthy as she had convinced herself it was. "Why don't you two stick around for awhile? I was going to make pasta for dinner tonight, and I could always use the company."

"I don't know how long we can-"

"Sounds great," interrupted Dean, smiling over at Jade. "I'll try getting in contact with Cas tonight, we can see what he can do, okay?"

Jade nodded, and for the first time in ages she felt hopeful. It suddenly struck her that perhaps all of this could have been solved much faster if she had just been honest with Dean, but from what Sam had told her about Dean's relationship with rationality, the two weren't very close. She rocked back and forth in her chair slightly, feeling like the entirety of herself was just a bundle of nerves.

"I am very sorry that I never told you Dean," she said quietly. "I just wanted to do what I thought would make Oliver happy, but I ended up dragging Sam into it and…"

"It's okay Jade," he said softly. He looked down at Oliver and took his hand gently. He missed the stupid jokes that Oliver would make, the silly way that he would try to flirt with Dean. He especially missed when Oliver wasn't just being silly. Yet it hit him that he and Oliver had only known each other for a few days at most. He certainly wanted to spend more time with him.

"Why don't we head back to my place and I'll get started on and you can contact Castiel," she said and stood up. Even if it was the only place where she could see her brother Jade hated hospitals. They were too clean and had too many bad memories in them. There was never enough quiet and it made her far too anxious to effectively function. Before getting a response from the other two she left, hands balled up in fists.

"So Cas, can you do it?"

"Dean it's more complicated than just tapping his forehead," Castiel said, his hands in his lap.

Despite repeated explanations from Sam and Dean, Jade had still put a plate of pasta in front of Castiel. She didn't want him to feel left out, even if he was an angel. "Why is it more complicated?"

"Your brother is deep in his own mind, like his soul doesn't want to be found," Castiel explained, speaking simply. After all she was only human. "The most I could do would to wake him up, but he wouldn't be there. He would still function, but just barely. Like a machine."

Jade nodded, knowing that anything like that wouldn't be her brother. He was made of passion and excitement and light. Barely doing anything wasn't something he was even capable of. "Is there anything we can do Castiel?" she asked softly, a sort of reverence in her voice.

"Keep praying I suppose," Castiel said. "Try talking to him more. Something that gets a more emotionsl response from him might be best."

At that Jade glanced over at Dean. If there was anyone that could get a strong emotional response from Oliver it was certainly Dean Winchester.

"What? Are you saying that me hitting on him is gonna make his soul get a hard on so he wakes up?" Dean asked, looking confused, disgusted, and overall shocked.

"Not necessarily, just any base emotion would do. Love even," Castiel said. "You don't need it to be sexual."

"Thank god because I never wanna see that shit," Jade said, then turned pink as she realized she had sworn in front of an angel.

"Yes… I need to be going, I wish you the best with your brother Jade," he said and nodded to her, before disappearing as if he had never been there.

"Well, at least we have some idea of what to do," Jade said, taking a bite of her pasta.

"Basically we have to convince you're entirely comatose brother that he should wake up with the power of love. Sounds like some hippie crap to me," Dean said and rolled his eyes, but it wasn't like they had an alternative.

"Maybe that other witch you know could help us out," Sam suggested.

"Marlow? Yeah, sure. We usually meet for dinner a few times a week so it won't be hard to see her," Jade said, nodding. "But she does tend to skip town if she even suspects there's danger, so maybe I should go alone. I mean she just disappeared last time…"

Sam pressed his lips into a thin line and nodded. "Alright. I'll go with Dean to the hospital then," he said and looked over at his brother, who seemed visibly uncomfortable with the idea of hot only flirting with a comatose man, but doing so in front of his brother.

"Why don't you just hang back Sammy? Watch the cats or something."

Sam made a noise that was somewhere between a gasp and a scoff and focused on eating. The rest of the night passed without incident, but the presence of Oliver was missed in every lull of conversation.

"You're still up too?" Sam said, walking over to where Jade was curled up on the couch. It was nearly two in the morning.

"Yeah, I usually text you until I fall asleep but uh… it's not like I can do that when you're just in the next room over, you know?" She tucked a lock of her hair behind her ear, and smiled at him weakly. She had what looked like a history textbook open in her lap. "Sit next to me, I want some company anyway."

Sam smiled at her and sat down, a little closer than necessary, but Jade only smiled at him. He noted just how small of a person she was, barely five feet tall, the way her black hair curled around her shoulder, and how her glasses seemed like they were at a risk of falling off of her nose at any minute. He moved just a bit closer, putting an arm around her shoulders.

Jade let out a small hum and leaned on him, using his chest as a sort of pillow. "You're warm," she said quietly, and seemed to be quite happy with this observation. Sam smiled down at her and just relaxed. It was rare they had the time to do this, to just enjoy a moment. It seemed they might be in town for at least a few weeks, he saw no reason not to enjoy it.

Absently, Sam traced patterns on Jade's arm. He smiled when she let out a happy hum and leaned into his touch. His actions got a bit more bold, and he ran his hand down her side, smirking when he elicited a gasp from her, making her stiffen. "Sam… how long until Dean figures it out?" she asked softly, looking up at him.

Sam shrugged. "We could just tell him you know. He won't die from finding out we're… what even are we?"

"Two people who have been texting and decided they liked each other a lot?"

"That does sound nice," he said and smiled down at her.

Jade couldn't help but laugh softly, just shaking her head as she walked to her room. It would certainly be an interesting time while the Winchesters were there.


	2. Chapter 2

"I'm not doing a spell to wake your brother up Jade, we know there isn't one that works," Marlow said, setting a hand on Jade's shoulder gently. "Sugar just let things take their natural course and you'll have him back eventually."

"Mars I'm not asking for you to completely wake him up, maybe just make it easier for him to wake up," Jade said, stepping closer to Marlow. "I just want it to be easier for him to hear us, Castiel said he's deep in his own mind. Don't you want to help Oliver?"

"Of course, but mixing magic and the mind can be dangerous. You understand, right?" Marlow said, clearing her throat a little. Even if she was being stubborn Jade was still her best friend. "I'll get you a spell that will make his soul more prone to persuasion, okay? But nothing more."

"Thank you," Jade said and gave her a tight hug.

"Yeah yeah, I'll drop it off at the hospital later, okay tiny?"

"I'll see you then," she said brightly. "Sam and Dean are staying with me for awhile, so Dean and I will be at the hospital."

"The hunters? Didn't Oliver have a thing for the shorter one?" Marlow said, tilting her head.

"Yeah, that's Dean. Oliver isn't subtle is he?"

"He never has been."

"Hey Dean, any news about Oliver?" Jade asked, sitting next to him and setting her purse down. A few hours had passed since her meeting with Marlow, and after running a few necessary errands she decided to join Dean at the hospital.

"No, nothing new," he said. "You know I don't really see why I would make more of an impact than you, I really haven't known him all that long."

"Honestly Dean, Oliver and I haven't been all that close until recently. I didn't see him for ten years once," she told him, turning to look him in the eyes. "So it doesn't surprise me a guy he knew for a collective week causes a more emotional response than me."

Dean recalled how when he first met Oliver neither of them could see their siblings. With Sam being away from him by choice he always thought it was the same for Jade. "He missed you."

"How do you know?" she asked, raising her eyebrows.

"We talked while he was doing my tattoo. It was years ago, and Sam and I… well let's say there was a pretty big fight and I was pretty sure we weren't gonna see him again. So we talked about that," Dean said and gave Jade a knowing look. "Trust me, he's your family."

"You don't know the half of what we've been through Dean," she said and let out a little laugh.

"He mentioned adopting you."

"Yeah, when I was seventeen. Some things happened, I'd honestly rather not talk about it," she said softly. "Marlow is coming by the way, there's a spell that makes his soul more accessible or some shit."

Dean nodded, shifting in his seat. He still wasn't entirely comfortable with using magic, but it wasn't like they had a cornucopia of options.

Marlow walked in, holding a basket in her arms. "Hey sugar, hi Dean," she said, setting the basket down on the table on top of Jade's books. "Okay so, I'm going to put turquoise around the room for healing, quartz to clear the mind, some yarrow for healing, calendula, oh and hyssop."

"Do you understand any of this?" Dean muttered, leaning over to Jade.

"Nope, but I trust what she does," Jade sad and shrugged.

"Alright sugar, that's all I can do for him right now," she said and sat by Jade and Dean. "It should help, make things clearer for him. When he does wake up, please call me. He"ll need some stuff to help him rest and recover."

"Isn't that what the coma is?" Jade asked. "Extreme rest and recovery?"

"He'll still need rest Jade, we're trying to take him out of it way too early," she said and folded her arms. "I'm not saying that I don't miss him, but this is selfish. You have to see that."

Jade looked away from her and focused on the ground. "Mars, Oliver is the only family I have, and he's important to more people than just me. I know this is stupid and probably wrong, but you really aren't the one to make that judgement."

Marlow nodded. "Just be careful honey, okay?"

Jade didn't respond, and eventually Marlow simply left.

"Let's get going Dean, let all this stuff work on Oliver for awhile," she said and stood up. "Can I grab a ride with you? I don't have a car, hospital bills and all."

Dean nodded, and the pair left.

Unbeknownst to them Oliver had stirred slightly. He wasn't awake yet, but something else was.

"All I'm saying is we could do something more productive than play Scrabble."

"Dean there isn't anything else to do," Sam said, leaned back on the couch. He had spent the day looking for a case to work, figuring that in between they could help with Oliver. "Trust me I looked."

"Are you sure? Because no offense to you Jade, but you and your brother have some boring interests," Dean said, to which Jade only responded with a shrug.

"You know Jade, I think I know the real reason why Dean doesn't like Scrabble," Sam said, looking over at Jade with a small smirk.

"And why is that Sam?"

"It's the big words, they stop him from winning," Sam said, looking back to Dean with a smirk.

"Oh screw you two," Dean said and waved his hand at them, although he was suppressing a smile.

Sam opened his mouth to make another jab at Dean, but was stopped by a knock at the door. "Jade was anyone supposed to come over?"

"No," she said and stood up, opening the door, freezing when she saw who it was. "Ollie? I didn't think…I thought it would be months!"

Oliver grinned, pulling his sister close and hugging her tightly. "Yeah, Marlow is a lot more talented than she realizes," he said, looking over Jade's shoulder to smile at Dean. "And of course hearing a friendly voice helped."

"I'd like to think I was a little more than just friendly," Dean said with a little smirk. He was shocked to see Oliver awake so soon, but happy nonetheless.

Oliver pulled away from his sister and sauntered over to the coffee table where they had been sitting. "So, Scrabble? Really Jade? Even I hate this game and I listen to classical music."

"Well we don't own any other board games," she said stubbornly, folding her arms. "Why don't you sit down, I'll get you some food. I need to call the hospital to find out why they didn't call me when you woke up."

"Oh, I snuck out," Oliver said with a smug grin. "Yeah they totally still think I'm in a coma."

"Why would you do that?" Dean asked, eyebrows pinching together.

"Because I missed all of you of course! All they're going to do is make me stay there another night, and probably make up some other issue I have so they can keep me longer," he said and rolled his eyes. "And then it'll cost more, and I have to wait even longer to get my hands on you." He took a small step closer to Dean, smirking slightly.

Dean cleared his throat a little, trying to avoid blushing at all. "Oliver, uh, Sam and Jade are still here you know," he said, gesturing vaguely to the other two in the room, who seemed a bit surprised.

"Right, right. Sorry about that Dean, I forgot how touchy you are," he said, rolling his eyes.

"Anyway," Jade said, hurriedly going to change the topic before anything else happened. "I have to call the hospital to tell them that you left since you're oh so special and think you're above everyone else."

"Aren't I better than everyone else?" Oliver said and batted his eyelashes.

"No," Jade said bluntly. Even if she was delighted to see her brother back home he had been nothing but cruel since he got there. "And I need to call Marlow too, she needs to give you some stuff to help with recovery. I'm sure she thought she'd be getting this call a lot later."

Oliver nodded a little and walked over to Dean, wrapping an arm around his shoulders. "So my buddy, pal, best friend I feel comfortable touching, how are you?"

"Well I came out to Sam so you can stop calling me pal," Dean said, the faintest of smiles on his lips. Maybe Oliver was just disoriented, he had just woken up from a long coma after all. "And you've been out about four months. So I missed you."

Oliver's eyes lit up as Dean spoke. "You came out? That's amazing," he said, trying to figure out how it went, but quickly figuring it out since Sam was there and didn't look angry or disgusted. It seemed to have gone much better than when Oliver had come out. He turned his face and buried it into the crook of Dean's neck, wrapping his arms around Dean tightly, just wanting to keep him close. "I'm so happy for you."

Dean smiled a little and held Oliver close, one hand on the back of his head. He ran his fingers through his hair gently, looking down at the other man with loving eyes. He guided them to the couch, just sitting down and keeping him close.

"Listen, Ollie, I'll go downstairs and make the calls, you relax," she said, looking at Sam and jerking her head for him to follow her downstairs.

"He's acting weird," she declared, once they were out of war shot. "When he was flirting with Dean in front of you, he wouldn't have done that unless he knew Dean was out, and breaking out of the hospital… god Sam what if something's wrong with him? Something even worse than a coma!"

"Hey, hey, calm down. He's probably just not thinking clearly, okay?" Sam said, frowning. However even he didn't believe the words leaving his lips. He hadn't known Oliver long, but this wasn't what he usually acted like.

Jade shook her head, tapping her phone against her lips and pacing back and forth, not saying anything else and just looking increasingly worried.

"Jade? Come on, it's your brother," he said, still doing his best to comfort her. "You have to know that."

"The only thing I know is that isn't Oliver."


	3. Chapter 3

Marlow was standing over Oliver, holding his chin up with a few fingers and shining a light in his eyes. "Well everything seems to be in order, it's not like you're a zombie or anything," she said, then tucked the utensil back into her pocket.

"I didn't die at any point, right?" he said, looking around at the gathered group. "Right?"

"We're pretty sure," Sam said and smiled.

"It seemed like you did for a moment though," Jade said, rubbing the back of her neck. "But Sam checked your pulse and you were fine, so I guess so."

Oliver nodded, pressing his lips into a thin line. Even if he was certain that he was himself he could feel the doubt radiating from his sister, and it hurt. She was his only family, the best family he could ever ask for, and she could barely stand to be near him.

"Alright sugar, seems like you're good to go. Guess I'm a better witch than I thought," Marlow said and let out a light laugh, patting Oliver's cheek.

"Oh come on Mars I've known you for years, you are my favorite witch," he said and stood up, stretching a bit. He turned to Dean, a sweet smile on his face. "Why don't the two of us go on a date? I mean there's no chaos, no dead bodies, a perfect time for some romance."

Dean laughed a little, smiling at Oliver. "Yeah, sounds good. Sam and I are going to be heading out soon, so I guess we should get this in while we can," he said and pecked Oliver's lips quickly.

"Aw, so soon?" Oliver said with a pout, wrapping an arm around Dean's waist. "I'm only teasing, I know you have to go, just don't forget about me." Oliver turned a little, waving over his shoulder to Jade, Marlow and Sam.

"So, where are we going?" Dean asked, moving away from Oliver so his hand moved from his waist once they were outside.

Oliver glanced down at his hand, wondering if there was something wrong with his touch, but it hit him that Dean was only newly out and he may not want to be too public yet. "How about a movie and then we can grab lunch? Just simple stuff."

"Simple? Sounds great."

"You know we could actually enjoy ourselves," Sam said, looking over at Jade. She had been going through books the entire time Dean and Oliver had been gone. "Seriously, just relax for a moment."

She looked up, just raising her eyebrows at him as if to tell him there was no way that was happening. It was almost silly, her clothes were slightly mismatched, and she was nervously biting her necklace. He sat down by her side and pulled her close. "Just trust me, I've been doing this for years, people just act differently when they've been through things. We both know that," he said, rubbing her arm.

"Sam, has Dean ever been through anything that changed him? Like you knew it wasn't right?"

There was plenty of that. Hell, possession, purgatory and more. Every time there was something that tipped Sam off, and every time people were telling him just to get over it. "Yes, but Jade he was just in a coma, Dean went through literal hell. I think it's a bit different."

"So you don't believe me either," she said and shifted away from him. "But… maybe you're right. After are you're leaving soon, let's just enjoy this."

Sam paused and then nodded, pulling her close again and leaning back. "Sometimes I think you look for an excuse to create drama," he said and looked down at her, keeping his tone light. "I mean not telling Dean about Oliver, thinking your brother has changed or something, but things are fine."

"Didn't Dean literally sell his soul when you died? I feel like he's a bit more over the top about stuff than me," she pointed out, laying her head on Sam's chest. "I mean I get it's only a coma, but he's crazier than me."

"There's a lot Dean has done, but it all works out in the end," Sam said, slightly more defensively than necessary. Maybe it was all the criticisms he heard, but everyone seemed to forget that they had saved the world more than once.

She nodded, just letting out a sigh and moving closer. "Can we talk about anything but our lives? I feel like I barely know you."

"What do you want to know?"

"Everything, but we can start small. What was your childhood like?" she asked, looking up at him with big eyes.

"Do you really want to know about that?" he asked, letting out a bitter laugh and looking down at her.

"Desperately," she said simply.

"Well it was mostly just moving around, motels and stuff. Sometimes we stayed places longer, and Dad would try to get us in school, but it was hard, you know? I never really had any roots except the impala," he said, absently stroking her back. "What about you? Things much have been pretty normal."

She let out a little laugh. "You'd think that," she said. "Up until I was eight Oliver lived with us, and then one day he just left. I mean he was sixteen, so I know there had to be a reason of some kind, but I don't ask. He always gets this sad look in his eyes whenever it even gets brought up. When I asked Mom or Dad…" She stopped, taking a little breath. "I feel like an idiot getting all emotional when I know you've been through worse."

"No, no it's fine," he said, sitting up a little. "What happened?"

"Mom would just get sad, Dad would get angry. Then Mom got cancer, she died when I was fourteen. Things got really bad then, Dad was angry all the time, but it got worse when he started to beat me. One night when I was seventeen I almost died," she said, now hugging Sam closer. "I woke up in the hospital, my dad was in jail, I was down two organs, and Oliver was sitting by me."

The two laid in silence, just holding each other. Both could only think of how much they had to learn about each other, and how hard that was going to be.

"So, how much longer are you going to be in town?" Oliver asked, sipping his drink. It was coke; Dean's was beer.

"Tomorrow, I found a case last night," Dean said, giving him a faint look of sadness. "I know it's pretty sudden but I have to get back out there."

"No, I know what you mean. I need to get back to running the shop, convince Jade that she can trust me again," he said and rubbed his face, seeming fairly exhausted for a man who had spent the last four months in a coma. "Anything interesting happen in the world while I was out?"

"Oh nothing much, world's still turning," he said and shrugged. "It was a little dull without you."

"And Jade was still being an idiot about just about everything. I can't believe she didn't tell you," Oliver said, shaking his head.

"Hey, I wouldn't say she's an idiot man, she was just trying to do what she thought was right," Dean said, frowning. "Listen, you're back now and that's all that matters."

Oliver shrugged, not speaking for awhile. "Let's head back to the shop, I should really see what's changed, do some damage control." He stood up, setting money for payment and a generous tip on the table. As he and Dean left the diner he left his hand open, simply there if Dean wanted to take his hand or leave it there. It was a simple gesture, and he was already slightly smiling when they left. However when he felt Dean take his hand there was no denying the grin on his face when he felt Dean take his hand. "I am never gonna get used to being seen with a guy like you," he said and looked over at Dean with warm eyes. "I mean just look at you!"

Dean rolled his eyes a little at that, although his face was flickering between a grim and the face he was trying to make to hide the grin. "You really are something man," he said, running his thumb over Oliver's knuckles gently. It felt nice, no it felt fucking fantastic, to walk down a street holding hands with a man he was falling for. His line of work didn't allow for close bonds frequently, but from what he had seen and heard Oliver could fend for himself pretty damn well.

As they arrived at the shop it was silent, even as they entered the apartment on the second floor. "Weren't Sam and Jade around here somewhere?" Dean said, looking around, then pausing when he saw the couch. "Well look at that, when do you think that happened?" He gestured to the pair who were asleep on the couch, holding on to each other.

"Getting together or passing out?" Oliver asked, raising his eyebrows. "Because I'm just a little more than happy that they're asleep, means they won't interrupt us."

"I thought you were just going through-" Dean was rapidly silenced by a deep and slow kiss from Oliver, who had one hand on the back of his head and the other slowly snaking down his back.

"That, I didn't want them to interrupt that," he said softly against Dean's lips, his eyes flashing up to Dean's to give him a little smirk. "That, and everything I am going to do to you."

The hunter smiled, setting his hands on Oliver's hips. "Then let's get started."

The next day in the early hours of the morning Dean was loading up the Impala. "So, you and Jade?" he said, smirking a little at his brother.

"Uh, yeah. She's different," he said as he climbed into the passenger's street.

Dean nodded as he started the car, smiling as the sound of music filled the car.

"Really? No rant on how dangerous it is, or how the job comes first?" Sam asked, raising his eyebrows.

"No, no. You're an adult, you make your choices. Besides, I'm not that much of a hypocrite," he said with a laugh as he pulled out of the driveway. "She's like over a foot shorter than you though, how does that even work?"

Sam rolled his eyes, letting out a laugh. "Yeah, I'm not telling you that," he said, shaking his head. "Ever."

"What? It's an honest question," he said, his lips flickering into a smirk. "I mean do you do some fancy positions or-"

Sam just rolled his eyes, grinning.

It was a long drive, and hours later they arrived in Kentucky, and started work on their case. It was basic, take out a vampire nest, save some people. It took less than a week, and it wasn't long before they were headed back to the bunker. Dropping off their bags and getting a moment to take a breath felt good.

Dean sat down on the couch, stretching out. He let out a low groan when his phone rang. "Hello?" he said in his usual gruff voice. It felt like his job was never ending, and there was a certain truth to that.

"Dean hi! Uh, how fast can you get here?" Jade said in a falsely bright tone. In the background he could hear a few loud thumps, and shouting.

"Jade? What's going on?" he said, standing up out of instinct.

Sam frowned, stepping towards his brother. Dean put her on speakerphone. "Jade are you okay?" Sam asked.

"For now. Listen you guys really need to get here, Oliver snapped. He's trying to break down the door and I really don't want to know what he has planned."

"Jade what the hell are you talking about?" Dean said, wondering if this was just some stupid joke the siblings were playing on him. After all Oliver was a softie, he couldn't hurt anyone.

"I don't know what's going on Dean. He's been acting weird, now his eyes went black and he's trying to fucking kill me," she said, voice growing more agitated. "Listen I would really appreciate it if I could get some help here, I'm not in the mood to die today."

"Jade it's gonna be awhile before we can get to you, can you get out?" Dean asked, already starting to walk outside with Sam following. "And are you sure that's what you saw? Black eyes?"

"Yes, it was fucking terrifying Dean! Get out? Yeah, I'll…" She stopped speaking and made a run for the window, opening it as fast as she could and climbing out, her calculated actions turning into frantic scrambling as Oliver got the door open, and instead of taking time with the ladder she just jumped, swearing when she hit the ground. "Well I'm out. I'll hide with a friend, I'll tell you where I am when you get here."

"Alright, just stay inside, don't talk to anyone. We'll be there as soon as we can," Dean said firmly, starting the car and peeling out of the driveway. He didn't want to believe what he had heard, but there was no way Jade was lying about this.


	4. Chapter 4

The next day Sam and Dean were sitting with Jade in the home of an unfamiliar witch, on the outskirts of the New Jersey suburb. Sam was sitting beside Jade, an arm wrapped around her. She was shaken, but better once they had arrived.

"Here, drink this," the witch said, handing Dean a drink.

"What is this?" he asked, holding up the teacup. It looked like something purple. "Some hippie fruit juice?"

The witch smiled, teeth bright white compared to their dark skin. "No, just a drink that'll make you feel better," they said warmly.

"You can trust them Dean, it's probably just going to make you feel better or something. Ash doesn't make malicious spells," Jade said, taking a cup and sipping the drink. "This is literally blueberry tea, isn't it?"

"Well, it makes people feel better," Ash said, setting the cups down. "I'll be in the basement if you need me."

"How do you know them?" Dean asked, just wanting to be sure that all bases were covered.

"Uh, old friend. They're dating Marlow," she said quietly, reaching over and taking Sam's hand. "Dean listen, Oliver completely lost it."

"No, no, Jade he's possessed. Whatever tried to attack you was not him," Dean said, shaking his head.

"But Dean it's weird, he acted normal then different, like he was fighting for control and didn't even know it," she said, bowing her head. "I'm scared that since he lost, he's gonna be gone forever."

"We'll get him back Jade," Sam assured her, patting her back. "We deal with people like this all the time."

"That's the same thing you said to assure me there wasn't anything wrong with Oliver, isn't it?" she said, voice cool. "It's not comforting Sam, I saw what you did to the poor guy that other demon possessed. You just stabbed him."

"We can perform an exorcism on Oliver, make sure he isn't hurt," Sam said, smiling weakly.

"Why didn't you do that to the other man?" she asked softly.

Neither sibling responded for a moment. "That man was corrupted," Dean said simply. "He was too corrupted, of we exorcised him he would have just died. We would have just wasted time."

Jade nodded, biting her tongue. She still thought they were just making excuses to not have done it. "So, Oliver… when could he have gotten possessed?" she asked, frowning. "I mean he was in a coma, could he get possessed then?"

"Maybe, demons don't really care about asking permission," Dean explained, eyes troubled. "They also aren't subtle, which is why it's so damn weird this only just happened."

"Dean I could tell something was off since he woke up, trust me," she insisted. "I mean he thought you weren't out and started saying that… Oliver is so damn careful about that stuff, he wouldn't have done that if he was himself."

The hunter looked at the ground, thinking back to the date he had gone on with Oliver, the night they spent together. It could have been with a demon and he didn't know. The very thought made him sick to the stomach. "Yeah, you're right," Dean said, voice rough. "Listen Jade, we'll go in, trap him, and perform an exorcism. Easy as pie."

"Right, I'm sure nothing ever goes wrong ever," Jade said, although it was gently teasing, not harsh. "Really though, Oliver will be okay?"

"I promise," Dean said.

"We'll go in tonight, so no one gets hurt," Sam said. "In the meantime we'll get ready, and get some rest."

"You could talk to Ash, they might have some stuff that you can use. They're really good at stuff that changes, like shifts," Jade said, wiggling her hand around in an attempt to demonstrate. "Could help if you wanted to get in without being recognized."

Dean nodded, standing. "Alright then, I'll see what we can do," he said, still not a fan of using a witch's spell in hunting. Still, he went downstairs where Ash was relaxing, or rather a woman who looked very much like Ash. "Excuse me?"

"Hello again," the woman said, smiling. "What can I help you with?"

"Uh, where's Ash? Are you their sister or..?"

The woman laughed a little. "No Dean, still Ash. I just alter myself to be more comfortable sometimes," she explained, gesturing to her body. "Sometimes I look like a man, sometimes a woman, sometimes in between or neither. Whatever feels right. I doubt you came down here to hear all about my gender, what can I do for you?"

"Jade mentioned you're good with magic that changes things," he said, realizing now why she was so talented with it.

"Right, and you need to get in undetected, to a store owned by one of the most paranoid witches in existence, now possessed by a crazy demon," she said, spinning on her heel and looking through some supplies. "In theory I could turn you into a squirrel."

"I know someone who would get a kick out that, but how would I get back? And I am not going to get turned into a squirrel," he said, jabbing his finger in the air near Ash.

"Not a fan of rodents I take it? I could cloak you. He would know the doors were opening and such, but the alarms in his head, and yes that's totally how it works, wouldn't go off unless he sensed humanoid movement," she explained. "So, I could cloak it and make you gave the essence of an animal, like a dog. You would need to go in on all fours though."

"You have got to be kidding me," he said and shook his head. "What else do I have to do, shake my butt and pant?"

"Only if you're into that sunshine," she teased, winking at him. "I'll get it done, but I'll only have one dose. You'll have to go in alone if you don't want anything to show."

That was a less than ideal plan. It was bad enough fighting a demon, but taking one on without Sam to back him up was idiotic and dangerous. They would need a plan. "Got it, I'll see you later then."

He went back upstairs, finding Jade and Sam sitting on the couch, Sam telling some story that was making Jade beam at him.

"He had that in his hair? That's disgusting!" she exclaimed, letting out a small giggle.

"Yeah, and the worst part was he just left it there the entire ride home," Sam said.

"Sammy," Dean said, cutting him for before he could continue. "Can we talk?"

"Yeah, hold on a moment Jade," he said, and she nodded to him. "What is it?"

"Ash said she has a spell that can hide is from Oliver's security, but only one of us," Dean said. "So I'm thinking I go in, set up a trap for it, then you go in to set off the alarm. That way it never even knows what hit it."

Sam nodded. "Sounds good."

"Oh and one more thing. If you tell anyone what I have to do for this spell to work, I will kill you," Dean said, setting a hand on his brother's shoulder. "And I mean that."

"What do you have to do for the spell?" Sam asked, raising his eyebrows.

"You'll see when you see," Dean said firmly. "Just never, and I mean never, tell anybody."

Sam raised his eyebrows and just nodded at Dean. "Sure man, I won't tell anybody."

Dean stared at him a moment longer, and once he was satisfied nodded to Sam and took a step back. "Good," he said.

Sam glanced over at Jade to give her a look, simply communicating that he had no idea what his brother was up to. He went back over to her, looping an arm around her hips and relaxing. "So, we have a few hours, what do you want to do?"

"We could watch some documentaries, some movies, or break the bed in Ash's guest room," she said, looking up at him and raising her eyebrows. "Take a wild guess which one I want to do."

Sam smiled a little, letting out a small surprised noise. "Let's get going then?" he said, grabbing her hand.

"Sounds fantastic," she said and kissed him, feeling blissful for a moment.

"You ready?" Dean asked, loading up the last of what they needed into the trunk of the car.

"Yeah. Are you going to be okay? I know you and Oliver are close," he said, eyebrows knitting together. "I could go in first you know."

"Okay, one, we aren't just close, he's my boyfriend, and two, no. I'm going in first, you second, that's what we planned," Dean said and got into the driver's seat, waiting only a moment for Sam to get in before he took off. He was focused on the task at hand, it would be simple. Things were never simple though. Instead of the usual stabbing they had to perform an exorcism, which seemed to be rarer and rarer as time passed, even if Sam was against it. Something inside of him ached though, at the thought of what Oliver was going through. Possession wasn't enjoyable in the least, and from what he had seen and heard, Oliver was just a sweet guy who turned out to be a witch. A sweet guy he had fallen hard for.

When they arrived he gazed at the shop, taking a moment to absorb all of it. The shop was decorated the way Oliver liked, so it looked complicated and messy with a secret order to it all. According to him it made him seem more ethereal to non magic users. Dean thought he just liked the look of it.

"Let's go then," he said, getting out of the car. He set a small pouch that Ash had given him in his mouth, rolling his eyes as he got down on all fours. He crawled up to the door, thinking of ways he could get back at the witch. He grabbed the door handle, shocked to find that it was unlocked. He opened the door, and the second he was within the bounds of the house he was thrown against the wall. His back hurt. His head hurt. Everything hurt.

"Hello Dean," the demon said, his eyes turning black. "Did you really think that I didn't expect you idiot hunters to show up? I mean you are so fucking predictable! Oh no, your precious little boyfriend is a demon now, just charge in like a dumbass! God you make this all so easy, and you couldn't even figure out when he got possessed could you?" He stepped forward, keeping Dean against the wall.

"Get the hell out of him you asswipe," Dean demanded, an animalistic growl emanating from his throat.

"Oh why would I? It's so fun in here," he said, letting out an almost delighted laugh. "Poor Oliver though, he's almost entirely broken. I mean when I took over he just kept telling me all about how you would save him, but he's quiet now. I don't think he believes in you anymore."

"Exorcizamus te, omnis immundus spiritus," Dean began.

"I wouldn't do that Dean. You see it was a mess when I possessed this idiot. He cast that spell to suck all his friend's souls out of me, and then you go idiots try to kill me. You see he was dying Dean, and when I jumped into his body I pushed his soul back in," the demon explained, grinning. "We're all tangled up in here, take out one and we both go down, but for your boy toy it's a bit more permanent."

Dean's eyes widened, and his voice trailed off. He was about to speak again, but Sam charged in, likely realizing this was taking far too long. "Dean!" he shouted, then shot the demon in the wrist. Normally it would be to the chest, but they needed Oliver to stay alive. Dean dropped to the ground as the demon released him.

"We need to go! Now!" Dean barked out, running for the door. The demon went to grab him, and missed.

Sam wanted to ask questions, but there was no time to, and it seemed to be only a second before they were driving away from the shop. "What the hell happened Dean?!"

"It knew we were coming," Dean said, gripping the steering wheel. "When I tried to exorcise it… fucking hell man it would rip Oliver's soul out."

"How is that even possible?"

"It went in as Oliver was leaving. It's the damn demon that was trying to become a god," Dean said, shaking with rage.

"Dean you realize what that means right?" Sam said, raising his eyebrows.

"Yeah it means I went on a date with a demon," Dean said, shaking his head.

"It means that spell killed Oliver," Sam said, letting out a long sigh. "Dean we have to talk to someone who knows about demons."

Dean glanced at Sam, confused for a moment, before he realized what he meant. "No! We are not calling Crowley!"

"Dean who else knows as much about demons? It's not like we have options."

They continued down the road, Dean fuming at the idea of having to call on the demon for help. "I mean he's the King of Hell," he said, slamming his hand down on the steering wheel as he pulled into the driveway.

"I know Dean, I don't like it either." Sam got out of the car, walking to the house. As they approached the house Jade opened the door just as they reached for it.

She looked behind them, and Dean looked down. "Oliver didn't… what happened?" she asked quietly.

"I'll explain inside," Dean said, his voice mournful.

It took about an hour for her to understand. When she finally did she said she was going to bed, and Sam went with her, after asking Dean if he would be all right. The two ended up holding each other for hours before falling asleep. When Dean was alone, he cried.


	5. Chapter 5

Dean was curled up beside Oliver, his face pressed into the crook of his neck. He felt warm and so damn safe for once in his life. Oliver was humming, trailing a finger up and down his back. "You were shaking Dean, what were you thinking about?" Oliver asked quietly, pulling Dean closer.

"It doesn't matter now," Dean said softly, leaving a few kisses on Oliver's neck before moving his head back a little to look at him. It was odd, he looked like such a soft person, yet Dean knew he could be tough as hell. "Wanna get up?"

Oliver shook his head, then looked up at Dean with eyes as black as midnight. "I don't want you to do anything ever again Winchester."

The dream still had Dean bothered while he sat with Sam and Jade that morning. "Man we have to figure this out soon," he said, taking a drink of his coffee.

"You know how we can," Sam said, folding his arms and raising his eyebrows.

The brothers were standing in a field, far enough away from the house that it couldn't be seen from where they were. Jade was nearby, gathering herbs Ash had asked for. "I still don't want to call him," Dean said, looking at Sam and shaking his head. He was still dialing the phone though. "Crowley, hi. We need a favor," Dean said, glancing at Sam.

"Really? And why on earth should I help you?" drawled the Scottish demon. "What's in it for me?"

"One of your demons is convinced he can become a god by eating human souls. Figured you might want a hand in stopping them," Dean said, avoiding his own desires in this. "Unless you're going soft that is."

At that the demon appeared in front of them. "Well, this is scenic," he said, looking around. "So, you can't handle this on your own? Don't you have that damn knife for a reason?"

"Well you see the demon is in this thing called a human," Dean responded, rolling his eyes. "If we exorcise it it'll rip out my friend's soul, it's all twisted together in there."

"Really? That's interesting," Crowley said and raised his eyebrows. "And you think I can do something about that?"

"Crowley you're our best bet. No one knows more about demons than a demon," Sam said.

"Then could I trust you two to do brain surgery just because you're human? Of course not you idiots!" Crowley spat out, narrowing his eyes at them. The brothers only folded their arms, clearly not buying it. "Fine. I can untangle the souls, but for a price."

Dean rolled his eyes, looking away for a moment, then back to the demon. "What do you want?"

"No more hunting demons," Crowley said simply. "Or I drag the soul you care so much about in that meat suit to the pits of hell and rip him apart until you can't recognize him."

"Excuse me?!" Dean said with a snarl, stepping forward and narrowing his eyes. "You have to be out of your damn mind!"

"How'd you know it was a him?" Jade asked, looking up from the bundle of plants in her hand. "Because last I checked no one told you that, so how did you know?"

"Who is this?" Crowley asked, looking at Dean and pointing at Jade.

"Not important, answer her question," Dean said, his voice growing darker.

"I guessed, sue me," Crowley said with a scoff, holding out his arms. "It was fifty fifty."

Dean was fed up, and grabbed Crowley, holding the knife under his chin. "You planned this didn't you?! Just so you could get under our skin," he said, pressing the knife to his skin a bit more. "Give me one reason to not kill you right now you sick son of a bitch."

"I actually can untangle the souls," he says, tilting his head up to avoid the point of the blade. "There will still be a price though."

Dean released him, rolling his eyes. "What now?" he demanded.

"The witch he's possessing has something I want, a book my mother seems to love," Crowley said, stepping back from Dean and touching his fingertips to his neck for a moment. "Not powerful, just sentimental. Figured it's a good trade, I betray my own kind for you and get a book in return. Seem fair?"

"Yeah," Dean said, his face dark. "So you're telling me all this bullshit is because you wanted some damn book?"

"What can I say? I love having something to hold over my mother," he said and shrugged. "And not originally, I spoke with Donnie, that's the demon in your precious witch friend, he was out of control. We both knew you'd end up doing something stupid and reckless to stop him, so I decided to use him for my own needs. Make sense Squirrel?"

"Plenty. Now get to work," Dean said, glaring at him.

"Fine, I'll get you what you need tomorrow. After that, I'll take my book and hopefully won't have to see you again for quite awhile," Crowley said, and with that disappeared, no trace of him ever being there.

"I hate that guy," Dean said, letting out a sound that was somewhere between a sigh and an angry grunt. "I mean jeez Sam he's been playing us for months."

Sam nodded, his jaw set. This had changed from serious enough already to a deal with the man ruling hell, and it was affecting more than just his brother and him. "I know, but I don't think we have a choice at this point."

The walk back to the house felt like a funeral march. Giving a book to the King of Hell never seemed like a good idea, even if he claimed it was just to bother his mother. More likely than not he would use it for some awful purpose that they would have to deal with later, and things would spiral rapidly. It seemed that was just the pattern of their lives.

"You guys done bringing demons onto my land?" Ash asked as they arrived, leaned against a post.

"Yeah," Dean said, his voice short, still angry. "Yeah I'm done with a lot of shit."

Even if the world was going crazy, the basics of life continued. That was how Sam and Dean ended up grocery shopping, not even a fifteen minute walk from the shop he knew a demon was pacing in.

Or, that he knew a demon was pacing in until he saw Oliver wandering around staring at avocados.

"Sam you see that?" Dean asked, jerking his head towards the possessed man who appeared to be testing the wrinkly green fruit for freshness. It wasn't typical demon behavior at all, unless it had a fondness for slimy green substitutes for mayonnaise. "That is not normal, I'm following him."

If no one had known Oliver was possessed this wouldn't have tipped them off. He was shopping, sticking mostly to vegetables, seeming unaware of the man following him around the store. That was until he turned suddenly to look at a bunch of grapes and came nearly face to face with Dean. For a moment his face was surprised, then it turned to delight. "Dean! I hoped I would see you."

Both Sam and Dean stared at him, their hands resting on their guns. "What the hell are you talking about?" Dean demanded, trying to hide the confusion that was bubbling up inside of him.

Oliver stood there, biting down on his lip. "Why don't we leave? I can explain," he offered, his face soft.

"Yeah I don't think so," Dean said, glaring. "Explain now."

"Dean it's me, okay? It's really me," Oliver said, pressing his lips together. "Sometimes I can control him more, press Adramelech down for awhile and just be a person." Adramelech. That was the name of the demon inside of him that he could feel clawing to the surface every moment that he existed as himself. It hurt to breathe, to smile, to go grocery shopping. Looking at Dean was its own living hell, but it was worth it.

Dean stared at him, clearly not believing him. "And do you have any proof of that, or am I just supposed to believe you?" he said, glaring.

Oliver faltered. "I don't have any Dean. I just… I'm me," he said, gesturing down to his body. "I know the date we went on, before Adramelech took over. You know the harsher things, those were him, but I don't have proof I'm me right now." He winced, realizing that he had about an hour before things went sour. "Listen, the next time I take over I'll call you, I'll… Dean, I'll use a code word. If you get a call and the first word isn't bright, then it isn't me. If it is, then it's me."

Dean still stared him, his eyes narrowed. "You understand I don't trust this, right?"

He nodded, his eyes trained on the ground. It was easier than making eye contact and hurting himself, easier than actually facing the hell that others were going through because of him. "Tell Jade I miss her, okay?"

"Sure,"Dean replied, voice lacking conviction and commitment. He watched Oliver carefully, until the witch walked away, seeing that there was no point to continue the borderline painful interaction.

"Dean do you think-"

"I don't know what the hell to think Sam, but he acted like Oliver," Dean said, unable to find even the slightest discrepancy in body language or mannerisms, but he hadn't been able to tell on their date either, while Oliver was battling for control. He didn't know what to think anymore. "Let's just get going Sam, we have everything we need." They most certainly didn't, but Sam wasn't going to argue with the way things had gone.

"So did you guys even try to get food or have you just decided you wanted to order out?" Ash asked, hands on their hips as they looked down at the pathetic amount of groceries.

"We ran into a problem at the store."

Sam gave Dean a withering look. "We ran into Oliver. Apparently he can take control for some amount of time, at least that's what he said. We aren't sure if it was actually him. There wasn't really any way we could prove it."

"Fuck dinner, I'm going to bed," Jade said, rubbing her face.

"I second that," Dean said, hating the idea of working with Crowley, and hating the fact he couldn't do a damn thing about it.


End file.
